Bruins GM, Peter Chiarelli traded Phil Kessel to the Toronto Maple Leafs on September 19th, 2009 for a first and second round pick in 2010 and a first rounder in 2011. This past June he used those picks to select Tyler Seguin and London Knight centre, Jared Knight, but it seems Chiarelli wants to trade this year's pick for someone who can help the Bruins right now.

Chiarelli was asked on WEEI radio in Boston if he'd consider trading Toronto's first round pick in 2011?
"Yeah, I'd look at it, sure. I've had discussions involving that pick. I certainly would look at it. We've got a lot of assets, so that alone allows us to be creative also … there's been one [deal] that we've thrown around here internally, I don't know that I would do it but it's something that warrants further discussion."

The last sentance is absolute brilliance on Chiarelli's behalf.

How often have fans lamented that their GM could have gotten more in return had he waited longer when trading away an elite asset. Oiler fans, and even Kevin Lowe himself, have wondered if he could have received more for Chris Pronger in the summer of 2006. (Back then he got Joffrey Lupul, Ladislav Smid and two first rounders and a 2nd. Today the trade has evolved into Jim Vandermeer, Smid, Jordan Eberle, Martin Marincin and Cam Abney).

Opposing GMs and Bruins' supporters wondered why then-GM, Mike O'Connell didn't let the rest of the league know he was shopping Joe Thornton. The Bruins got fleeced in that deal getting only Wayne Primeau, Brad Stuart and Marco Sturm.

Clearly Chiarelli wants everyone to know where he stands with his "bonus" pick.

Chiarelli's comments make it clear the Leafs' pick is in play, but the subtle hint that he is close to a trade will surely get every other GM's attention. Right now the pick would be the 5th choice, and at the very least it will be in the top-eight. Chiarelli is in a great position. His team is competitive, they already have a potential star in the system, Seguin, from the original deal, and now by going public he has increased his chances of maiximizing his return.

With 20 days until the trade deadline, this simple quote will have fans in every market looking at potential deals that could help their team.

COUCH GM

While every team would love a shot at a top-five pick, the reality is there might only be a handful of teams who are willing, and able, to offer up a fair package.

Ottawa, Toronto, Florida, New Jersey, the Islanders and Edmonton are either completely out of the playoff race or hanging by a thread like Buffalo, Columbus and St. Louis. There are many teams currently in the hunt for the postseason, but would any of their GMs be willing to sacrifice this season for a potential top-five pick?

According to Capgeek the Bruins can "currently" only acquire a max cap hit of $2.9 million, so I'm assuming any trade they make will see Michael Ryder, and his $4 million cap hit, as part of the package going the other way.

EDMONTON: The Oilers are currently 30th, and Steve Tambellini would be willing to part with a proven player to secure a second top-five pick in June. Ales Hemsky and Dustin Penner are the only Oiler veterans that would grab Chiarelli's attention. Chiarelli acquired Nathan Horton and Gregory Campbell for Dennis Wideman and the 15th pick last summer, so it might take more than just Hemsky or Penner to get the pick. I suspect Chiarelli will want some sort of young prospect to be added to any deal.

OTTAWA: I know it would be within the division, but Chiarelli had no problem making the original deal with Toronto, so I don't see him shying away if the Sens put a good deal on the table. Chris Phillips is the obvious name to be part of the package, but the Sens would need to add much more. Would Mike Fisher entice Chiarelli? I don't think so, because he has two years left at $4.2 million, but Bryan Murray should be trying to save his job by securing another top-five pick.

New Jersey: Despite their recent hot streak, they aren't going anywhere, and you wonder if Lou Lamoriello wants to break up his team rather than see them drop out of the bottom five. Lamoriello's problem is he doesn't have anyone who financially fits with the Bruins. Elias and Rolston are too expensive, and past their prime. Would Lou gamble and move Travis Zajak and David Clarkson? Zach Parise is up for a big raise, so the Devils need to make some room.

FLORIDA: Chiarelli and Dale Tallon made a deal at the draft, but I'm not sure they can come up with another one. The Panthers only have veterans Weiss, Booth, Olesz, Wideman, Kulikov, Clemmensen and Bryan Allen under contract for next season. Bryan McCabe, Cory Stillman, Radek Dvorak and Chris Higgins won't get you a top-five pick. I don't see Florida being a partner.

NY ISLANDERS: Garth Snow wouldn't move John Tavares, and after that he doesn't have anyone who could help the Bruins playoff push. Marc Streit and Trent Hunter are hurt, and the rest of the lineup is too inexperienced.

TORONTO: You know that Brian Burke will call Chiarelli and see if he is interested in making another deal, and if I'm Chiarelli I'd be all ears. I loved the deal he pulled off in 2009, but this time Burke's cupboard is a tad bare. I'm sure Tomas Kaberle's name will be first out of the gate, like it has been for the past two years. Would Kris Versteeg and Kaberle be enough?

BUFFALO: Sabres new owner, Terry Pegula, has a reputation of being very aggressive, but Darcy Regier hasn't been that way in his tenure in Buffalo. The Sabres, after their win Tuesday, are only four points out with two games in hand. I'll bet Pegula would rather make the playoffs this year, and if they stay close in the next few weeks, I think they'll be more of a buyer than a seller.

ST. LOUIS: Most of the Blues best players are young, and moving one of them for another top-five pick would seem like a lateral move. The Erik Johnson trade rumblings don't make sense, especially for a draft pick. I don't think Andy MacDonald and Eric Brewer would entice Chiarelli and I doubt the Blues would move one of Oshie, Perron or Backes.

COLUMBUS: The Jackets have won three straight and are only four points behind 8th place Calgary with two games in hand. GM, Scott Howson's job is on the line if he misses the playoffs, so I don't see him trying to build a future that he won't be a part of. I see Howson as a buyer, especially if the Jackets are within four points or less.

OTHER POSSIBILITIES

CALGARY: The Flames are 11-3-4 since Darryl Sutter resigned got fired, and suddenly in the playoff picture. Would Jay Feaster roll the dice and trade Robyn Regehr, and hope his team could still make the playoffs and get a top pick? The Flames are in a tough spot. They don't have much depth in the farm, but would Feaster, or more specifically the owners, be willing to sacrifice a few home playoff dates for a potential franchise player? Tough call.

MINNESOTA: The Wild haven't had a first round pick pan out since they took Brent Burns 20th in 2003. Since Burns they've drafte AJ Thelan (12th, 2004), Benoit Pouliot (4th, 2005), James Sheppard (9th, 2006), Colton Gillies (16th, 2007), Tyler Cuma (23rd, 2008), Nick Leddy (17th, 2009) and Michael Granlund (9th, 2010). Granlund and Leddy are too young to judge yet, but the rest are more suspects than prospect at this point. Chuck Fletcher needs to make a splash, and I wonder if Nick Schultz and Matt Cullen would get Chiarelli's attention.

I'm sure many other GMs will contact Chiarelli to find out his asking price, and after yesterday's comments I'm sure Chiarelli's phone will be ringing frequently.

Letting the entire league know that a potential top-five pick is on the market was a savvy move by Chiarelli, and I won't be surprised if he ends up getting more than the supposed offer that is currently on the table. The only negative might be that the current GM that he is dealing with gets annoyed and backs out.

Chiarelli likely weighed the options and realized, that in this case, a public auction will garner a higher price than what he would have got in a silent one.

Brilliant move.

One of Canada's most versatile sports personalities. Jason hosts The Jason Gregor Show, weekdays from 2 to 6 p.m., on TSN 1260, and he writes a column every Monday in the Edmonton Journal. You can follow him on Twitter at twitter.com/JasonGregor

The capgeek figure includes Marc Savard, who I think will be moving to LTR, though I might be mistaken. Personally, I'd rather have hemsky or Penner than Cullen and Schuktz, but maybe I'm a homer.Fun days to be Chiarelli, its gonna be like picking from a buffet.

When you read about what the teams have to offer.....no one compares to what the oilers have. I think Fisher is the only guy that would draw interest from Ottawa but Boston needs scoring and I don't think fisher is that guy. He's a properly paid Horcoff. Boston's got their guy in that role in Bergeron

Edmonton has skilled forwards and can eat cap space for teams if it helps their future.

Hemsky/Vandermeer (Boston isn't deep on D if they're making a serious run)

For

1st/Ryder + another salary dump

Keeping in mind that toronto's pick isn't likely to be a lottery pick (likely 5-10). Hemmer is a proven "star". Edmonton can't get too carried away. Tambo earns his legacy this year because this will shape the team and he can't ask MBS to do the trades for him.

Gregor: Do you figure that the young asset you speak of coming from the Oilers would be in the caliber of a young gun currently with the team, or in the prospect pool. If it is a player on the team I would see that as somewhat of a lateral move but curious to see what you think. Seems to me as if the kids with the club right now should figure heavily in the future direction of the team.

The capgeek figure includes Marc Savard, who I think will be moving to LTR, though I might be mistaken. Personally, I'd rather have hemsky or Penner than Cullen and Schuktz, but maybe I'm a homer.Fun days to be Chiarelli, its gonna be like picking from a buffet.

You are correct and that is why I put "currently" since it could change before Feb 28th.

I think Schultz is underrated as a D-man, and the Bruins need more blueline depth heading into the playoffs.

Gregor: Do you figure that the young asset you speak of coming from the Oilers would be in the caliber of a young gun currently with the team, or in the prospect pool. If it is a player on the team I would see that as somewhat of a lateral move but curious to see what you think. Seems to me as if the kids with the club right now should figure heavily in the future direction of the team.

Not a young guy like Hall, Eberle, Omark or Paajarvi, but someone in the organization is what I meant. Just assuming Chiarelli might want something else, just in case Penner or Hemsky don't re-sign there after next season.

I don't want the Oilers to trade Penner and Hemsky. Especially not when they are still signed for 1 more year. Especially when the kids still need sheltering next year. Especially when there's still a chance they can be extended. Especially for a pick that might not even be in the top 8. Especially in a rather weak draft year. Especially when we will already get a top 3 pick of our own.

No thanks.

If Burkie has taught us anything, DO NOT trade with this "genius". You'll likely get fleeced.

Oilers should see if they can get Rishaug to do another story. A mock of Chiarelli where Tambo comes out stating that he is indeed thinking about trading Sheldon Souray. He's had a couple offers already that just need to be signed in summer, he just doesn't want to hurt his development in the A that he's been getting. He's a true leader and really taking responsibility in driving the team bus!

The Flames could offer Chiarelli the once-in-a-lifetime deal of Sarich AND Hagman for only one Toronto 1st round pick! Act now, and they'll throw in Kotalik (4 points in 4 games in the AHL) at absolutely no extra cost.

Is letting the league know that a player or pick is available really considered a brilliant move? I'd say not letting it be known is absolutely asanine and ridiculously stupid. On the occasion when the media isn't getting a hold of the information I'm still sure a gm shops their availability list.

In regards to the Joe Thornton trade, "absolutely asinine and ridiclously stupid."

It would be nice to gain TO's pick from Boston, but I'd like to see any kind of deal with Atlanta go first. Athough a top 10 pick would be right for the Oiler's "rebuild", I'd like to see a few prospects gained in return via trade opposed to drafting and developing....mostly cause I'm impatient and want success next year not in 5.lol. Sell Penner high!!! I doubt he'll resign and we can get highest value now, opposed to seasons 2006-2008 in comparison IMO

I'm not sure Brian Burke's stupidity equals Chiarelli's genius. Other than that you make a good point. I just hope Tambellini doesn't stumble into someone elses bear trap. Between his deals and Kevin Lowe's deals I am far from comfortable with their combined judgement on pro trades. The only reason for hope for the Oil currently is MacGregor's minor league drafting and not much is proven on any of his changes so far due to the early stages of the player's growth.

In my dream world the Flames would send Bourque, Saarich, + a pick (if they had to and not a first rounder) to pry Bogosian out of Atlanta. Then maybe they could make the deal for Regehr to Boston for the first rounder. Calgary could take Ryder back as a salary dump and maybe throw in a pick or prospect to compensate. That would be about $11 million out and a little under $7 million coming back. Giving Calgary a much needed $4 mill in breathing room.

You are correct and that is why I put "currently" since it could change before Feb 28th.

I think Schultz is underrated as a D-man, and the Bruins need more blueline depth heading into the playoffs.

It will be interesting to see what offer, if any, he accepts.

Schultz is a big time underrated d-man. When ever i have watched wild games or highlights i always notice him and the solid game he plays. I look for him specifically because i used to live with his cousin in university, so maybe i have a bit of a bias there. But i have always thought he was a solid d-man.

I'm jumping on the Bogosian train, although I don't think Hemskey or Penner would be enough. ATL is most likely not making the playoffs this year so they would only have either signed for one year. I think the player ATL would take is Gagner. It would be a trade for a young asset for another young asset and fill the needs of both teams, we have too many small forwards and need better D. This would also free up Tambi to draft one of the young centermen (RNH) who would slide into the second line behind Horc for a few years.

i think we need a top centermen desperately, and if we trade to boston and get TO pick we probably won't get couturier or nugent - hopkins. I think trade hemsky, penner, and possibly cogliano to l.a for brayden shenn and get something else in return and then draft larsson at the draft. I think that would be the smartest thing because we now have a top centermen and top defencemen. also reading your latest blog we have a lot of good forwards coming up.

So what exactly happens when that pick ends up being closer to a top 10 pick than a top 5 pick? Not sure I really want to give up either Hemsky or Penner for a top 10. Too much risk. I do however think if we have any intention at moving either guy, that we do it this year.

Very few guys around this year for trade and I really don't want to risk Hemsky going down next season and getting nothing for him.

It would be really nice if we could get more out of the Bruins if we have to bring Ryder back here. Jordan Caron could be big body RW, Adam McQuaid a big stay at home defender, or even Colborne for our big center.

It might be asking too much, but I think we are dealing from a position of strength when our 2 players we are moving both have a year left on their deals. We haven't been in the driver's seat on many deals in the past.

If the Leafs re-acquired their own 2011 pick for the package Gregor mentions, then the entire deal boils down to:

To Toronto: KesselTo Boston: Seguin, Knight, Versteeg, Kaberle

Even though both separate transactions might have looked somewhat plausable as individual deals at the time they were made, when you put them together (and every MSM and fan in North America will do just that) and look at them in hindsight, it's just so lopsided as to be laughable.

Burkie has to deal with the fact that this one didn't swing his way. Trying to 'fix' it now will only make it worse and could cost him his job.

So what exactly happens when that pick ends up being closer to a top 10 pick than a top 5 pick? Not sure I really want to give up either Hemsky or Penner for a top 10. Too much risk. I do however think if we have any intention at moving either guy, that we do it this year.

Very few guys around this year for trade and I really don't want to risk Hemsky going down next season and getting nothing for him.

Do you think Magnus Paajarvi has more upside than Penner or Hemsky? He was a 10th pick.
Sure it might be a gamble, but if Penner or Hemsky don't want to be here past next season, you need to get something for them.

It would be nice to gain TO's pick from Boston, but I'd like to see any kind of deal with Atlanta go first. Athough a top 10 pick would be right for the Oiler's "rebuild", I'd like to see a few prospects gained in return via trade opposed to drafting and developing....mostly cause I'm impatient and want success next year not in 5.lol. Sell Penner high!!! I doubt he'll resign and we can get highest value now, opposed to seasons 2006-2008 in comparison IMO

In a perfect world the Oilers could perhaps do both!

If there is legs to the Atlanta deal with Bogosian, Hemsky would be the main target for them. Not sure how and what would have to be in this deal but it is possible. Any ideas?

Penner would be Boston's target not Hemsky. Would a Penner/Gilbert/Calgary's 3rd for Toronto's #1/Colbourne/Ryder be close. As mentioned here already, Ryder could be flipped for a pick. It is a contract year for him and as usual he is scoring again. He could add supplemental scoring for a playoff bound team.

Cap space works for all teams infact Boston would still have roughly 2.9 to spend to fill in this year.

I think Burke only made that deal because he wanted to sign Kessel as an RFA but couldn't because of the optics, given his ridiculous reaction to Lowe signing Penner, the old cutting off the nose to spite the face.

While Hemsky and Penner may be better than most 5th overall picks, the simple fact is that they may not be here when it's finally time for the Oilers to compete. Trading them at their maximum value, whether that value is less than their current abilities (i.e. a 5th overall pick), is a good move, especially since at this time, their skills aren't helping the Oilers make the playoffs.

Do you think Magnus Paajarvi has more upside than Penner or Hemsky? He was a 10th pick.
Sure it might be a gamble, but if Penner or Hemsky don't want to be here past next season, you need to get something for them.

That's the crux of it really.

Tambo needs to figure out before the deadline if Penner and Hemsky will sign extensions on July 1.

If they will, they're off the table baring a massive overpay.

If they won't, now is the time to move them, and you need to make sure you get a lot more than a deal centered around Nilsson or Lupul....

Do you think Magnus Paajarvi has more upside than Penner or Hemsky? He was a 10th pick.
Sure it might be a gamble, but if Penner or Hemsky don't want to be here past next season, you need to get something for them.

Magnus might have more offensive upside then Penner, but I doubt he has more offensive upside then Hemsky.

A quick scan of 5-10 picks however shows your odds of getting a player superior to Hemsky/Penner in those slots really isn't that good.

Of course your last sentence is key though, if they aren't planning on sticking around (for a resonable price) then the team needs to get something for them... if a 5-10 pick is the best we can do, then so be it.